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Structure-activity relationships of the estrogenic sesquiterpene ester ferutinin. Modification of the terpenoid core

Appendino, G; Spagliardi, P; Sterner, Olov LU and Milligan, S (2004) In Journal of Natural Products 67(9). p.1557-1564
Abstract
Esterification of p-hydroxybenzoic acid, a very weak estrogenic compound, with the daucane alcohol jaeschkeanadiol (1b) leads to a spectacular magnification of the estrogenic activity. To identify the structural elements responsible for this effect, the terpenoid core of jaeschkeanadiol p-hydroxybenzoate (ferutinin, 1a) was modified, capitalizing on the presence of two functionalities, the monoacylated, hydrogen-bonded 1,3-diol system and the double bond. The hydrogen bonding, while possibly useful, was not critical for activity, while hydrogenation and cyclopropanation of the double bond were tolerated. Conversely, oxidative modifications of the double bond that placed a hydroxyl on the a-face of the molecule proved detrimental. Taken... (More)
Esterification of p-hydroxybenzoic acid, a very weak estrogenic compound, with the daucane alcohol jaeschkeanadiol (1b) leads to a spectacular magnification of the estrogenic activity. To identify the structural elements responsible for this effect, the terpenoid core of jaeschkeanadiol p-hydroxybenzoate (ferutinin, 1a) was modified, capitalizing on the presence of two functionalities, the monoacylated, hydrogen-bonded 1,3-diol system and the double bond. The hydrogen bonding, while possibly useful, was not critical for activity, while hydrogenation and cyclopropanation of the double bond were tolerated. Conversely, oxidative modifications of the double bond that placed a hydroxyl on the a-face of the molecule proved detrimental. Taken together, these observations identified the substitution at C-8/C-9 as critical for activity. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Natural Products
volume
67
issue
9
pages
1557 - 1564
publisher
The American Chemical Society
external identifiers
  • pmid:15387659
  • wos:000224187700023
  • scopus:4644311704
ISSN
0163-3864
DOI
10.1021/np049796w
language
English
LU publication?
yes
id
d1f05737-d4eb-4889-acca-dd9a5c4678ba (old id 141154)
date added to LUP
2007-07-10 08:27:22
date last changed
2017-11-19 04:15:33
@article{d1f05737-d4eb-4889-acca-dd9a5c4678ba,
  abstract     = {Esterification of p-hydroxybenzoic acid, a very weak estrogenic compound, with the daucane alcohol jaeschkeanadiol (1b) leads to a spectacular magnification of the estrogenic activity. To identify the structural elements responsible for this effect, the terpenoid core of jaeschkeanadiol p-hydroxybenzoate (ferutinin, 1a) was modified, capitalizing on the presence of two functionalities, the monoacylated, hydrogen-bonded 1,3-diol system and the double bond. The hydrogen bonding, while possibly useful, was not critical for activity, while hydrogenation and cyclopropanation of the double bond were tolerated. Conversely, oxidative modifications of the double bond that placed a hydroxyl on the a-face of the molecule proved detrimental. Taken together, these observations identified the substitution at C-8/C-9 as critical for activity.},
  author       = {Appendino, G and Spagliardi, P and Sterner, Olov and Milligan, S},
  issn         = {0163-3864},
  language     = {eng},
  number       = {9},
  pages        = {1557--1564},
  publisher    = {The American Chemical Society},
  series       = {Journal of Natural Products},
  title        = {Structure-activity relationships of the estrogenic sesquiterpene ester ferutinin. Modification of the terpenoid core},
  url          = {http://dx.doi.org/10.1021/np049796w},
  volume       = {67},
  year         = {2004},
}